Ifetroban sodium | CAS# 156715-37-6 | TxA2/PGH2 receptor antagonist

MedKoo Cat#: 576592 | Name: Ifetroban sodium

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ifetroban, also known as BMS-180291, is a potent and selective TxA2/PGH2 receptor antagonist. Ifetroban reduces coronary artery dysfunction in a mouse model of Duchenne muscular dystrophy. Ifetroban has been studied in animal models for the treatment of cancer metastasis, myocardial ischemia, hypertension, stroke, thrombosis, cardiomyopathy, and for its effects on platelets.

Chemical Structure

Ifetroban sodium

CAS#156715-37-6 (sodium)

Theoretical Analysis

MedKoo Cat#: 576592

Name: Ifetroban sodium

CAS#: 156715-37-6 (sodium)

Chemical Formula: C25H31N2NaO5

Exact Mass: 462.2131

Molecular Weight: 462.52

Elemental Analysis: C, 64.92; H, 6.76; N, 6.06; Na, 4.97; O, 17.30

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

156715-37-6 (sodium) 143443-90-7 (free acid)

Synonym

Ifetroban sodium; BMS 180291-02; BMS-180291; BMS180291;

IUPAC/Chemical Name

Benzenepropanoic acid, 2-((3-(4-((pentylamino)carbonyl)-2-oxazolyl)-7-oxabicyclo(2.2.1)hept-2-yl)methyl)-, monosodium salt, (1S-(exo,exo))-

InChi Key

WOHSQDNIXPEQAE-QBKVZTCDSA-M

InChi Code

InChI=1S/C25H32N2O5.Na/c1-2-3-6-13-26-24(30)19-15-31-25(27-19)23-18(20-10-11-21(23)32-20)14-17-8-5-4-7-16(17)9-12-22(28)29;/h4-5,7-8,15,18,20-21,23H,2-3,6,9-14H2,1H3,(H,26,30)(H,28,29);/q;+1/p-1/t18-,20-,21+,23-;/m0./s1

SMILES Code

[Na+].CCCCCNC(=O)c1coc(n1)[C@H]2[C@@H](Cc3ccccc3CCC(=O)[O-])[C@@H]4CC[C@H]2O4

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 462.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Laidlaw TM, Buchheit KM, Cahill KN, Hacker J, Cho L, Cui J, Feng C, Chen CC, Le M, Israel E, Boyce JA. Trial of thromboxane receptor inhibition with ifetroban: TP receptors regulate eicosanoid homeostasis in aspirin-exacerbated respiratory disease. J Allergy Clin Immunol. 2023 Apr 15:S0091-6749(23)00457-8. doi: 10.1016/j.jaci.2023.03.030. Epub ahead of print. PMID: 37068712. 2: Mitchell R, Frederick NE, Holzman ER, Agobe F, Allaway HCM, Bagher P. Ifetroban reduces coronary artery dysfunction in a mouse model of Duchenne muscular dystrophy. Am J Physiol Heart Circ Physiol. 2021 Jul 1;321(1):H52-H58. doi: 10.1152/ajpheart.00180.2021. Epub 2021 May 28. PMID: 34048282. 3: Pestel S, Nath A, Jungermann K, Schieferdecker HL. Inhibition of prostaglandin D2 clearance in rat hepatocytes by the thromboxane receptor antagonists daltroban and ifetroban and the thromboxane synthase inhibitor furegrelate. Biochem Pharmacol. 2003 Aug 15;66(4):643-52. doi: 10.1016/s0006-2952(03)00398-8. PMID: 12906929. 4: Rosenfeld L, Grover GJ, Stier CT Jr. Ifetroban sodium: an effective TxA2/PGH2 receptor antagonist. Cardiovasc Drug Rev. 2001 Summer;19(2):97-115. doi: 10.1111/j.1527-3466.2001.tb00058.x. PMID: 11484065. 5: Dockens RC, Santone KS, Mitroka JG, Morrison RA, Jemal M, Greene DS, Barbhaiya RH. Disposition of radiolabeled ifetroban in rats, dogs, monkeys, and humans. Drug Metab Dispos. 2000 Aug;28(8):973-80. PMID: 10901709. 6: Katz SD, Radin M, Graves T, Hauck C, Block A, LeJemtel TH. Effect of aspirin and ifetroban on skeletal muscle blood flow in patients with congestive heart failure treated with Enalapril. Ifetroban Study Group. J Am Coll Cardiol. 1999 Jul;34(1):170-6. doi: 10.1016/s0735-1097(99)00180-1. PMID: 10400007. 7: Johnson RA, Belmonte A, Fan NY, Lavesa M, Nasjletti A, Stier CT Jr. Effect of ifetroban, a thromboxane A2 receptor antagonist, in stroke-prone spontaneously hypertensive rats. Clin Exp Hypertens. 1996 Feb;18(2):171-88. doi: 10.3109/10641969609081763. PMID: 8868999. 8: Gomoll AW, Schumacher WA, Ogletree ML. Dose-related cardioprotection by ifetroban in relation to inhibition of thrombosis and ex vivo platelet function. Pharmacology. 1995 Feb;50(2):92-110. doi: 10.1159/000139271. PMID: 7716179. 9: Gomoll AW, Ogletree ML. Failure of aspirin to interfere with the cardioprotective effects of ifetroban. Eur J Pharmacol. 1994 Dec 27;271(2-3):471-9. doi: 10.1016/0014-2999(94)90808-7. PMID: 7705447. 10: Gomoll AW, Grover GJ, Ogletree ML. Myocardial salvage efficacy of the thromboxane receptor antagonist ifetroban in ferrets and dogs. J Cardiovasc Pharmacol. 1994 Dec;24(6):960-8. doi: 10.1097/00005344-199424060-00014. PMID: 7898080. 11: Lodge NJ. Direct vasoconstrictor effects of sandimmune (cyclosporine A) are mediated by its vehicle cremophor EL: inhibition by the thromboxane A2/prostaglandin endoperoxide receptor antagonist ifetroban. J Pharmacol Exp Ther. 1994 Nov;271(2):730-4. PMID: 7965789.